Issue 17, 2014

Benzofuranquinones as inhibitors of indoleamine 2,3-dioxygenase (IDO). Synthesis and biological evaluation

Abstract

A series of benzofuranquinones, analogues of the marine metabolite annulin A, has been synthesized and evaluated as inhibitors of human indoleamine 2,3-dioxygenase (IDO). The synthesis was carried out by copper(II)-mediated reaction of bromobenzoquinones with 1,3-dicarbonyl compounds followed by functional group interconversions. The most potent compounds were 5-methoxy-2-methylbenzofuranquinones containing a CH2OR group at position-3 with IC50 ∼ 0.2 mM. The corresponding hydroquinones were inactive. Compounds based on the benzimidazolequinone framework are also active IDO inhibitors. The quinones do not generate significant levels of oxidative stress at concentrations that inhibit IDO.

Graphical abstract: Benzofuranquinones as inhibitors of indoleamine 2,3-dioxygenase (IDO). Synthesis and biological evaluation

Supplementary files

Article information

Article type
Paper
Submitted
13 Nov 2013
Accepted
20 Feb 2014
First published
21 Feb 2014

Org. Biomol. Chem., 2014,12, 2663-2674

Benzofuranquinones as inhibitors of indoleamine 2,3-dioxygenase (IDO). Synthesis and biological evaluation

C. Carvalho, D. Siegel, M. Inman, R. Xiong, D. Ross and C. J. Moody, Org. Biomol. Chem., 2014, 12, 2663 DOI: 10.1039/C3OB42258E

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